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Method for synthesis of 2-imino oxazole

A technology of iminooxazole and synthesis method, applied in the direction of organic chemistry and the like, can solve the problems of few 2-iminooxazole synthesis methods, complicated substrate preparation, low reaction yield and the like, and achieve the target product yield High, cheap and easy to obtain raw materials, high product yield effect

Inactive Publication Date: 2017-05-31
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the above-mentioned methods often have harsh conditions, low reaction yield, complicated substrate preparation, and a certain amount of transition metal catalyst, which makes its application in the synthesis of 2-imino oxazole derivatives subject to certain restrictions. limit
[0004] Given that there are fewer and less efficient synthetic methods for 2-iminooxazole

Method used

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  • Method for synthesis of 2-imino oxazole
  • Method for synthesis of 2-imino oxazole
  • Method for synthesis of 2-imino oxazole

Examples

Experimental program
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Effect test

Embodiment 1

[0039]

[0040] In a sealed 10 mL tube, add 1-phenyl-3,3-dianiline-2-propen-1-one 2a (94 mg, 0.3 mmol), iodophenyl acetate PhI(OAc) in sequence under air 2 (116mg, 0.36mmol), potassium carbonate K 2 CO 3 (83mg, 0.6mmol) and 2.5mL of dichloromethane were stirred at 80°C for 2 hours. After cooling to room temperature, filter through diatomaceous earth, remove volatile components under reduced pressure, and then separate by silica gel column chromatography (eluent is petroleum ether (60-90°C) / ethyl acetate / dichloromethane, v / v / v=15:1:1), the target product 1a (69 mg, yield 74%) was obtained, and the target product was confirmed by nuclear magnetic resonance spectroscopy.

Embodiment 2

[0042] Reaction steps and operation are with embodiment 1, and difference with embodiment 1 is that oxygenant is trifluoroacetic acid iodobenzene PhI (TFA) 2 . The reaction was stopped, and the target product 1a (9 mg, yield 10%) was obtained after post-processing. It shows that iodobenzene trifluoroacetate can also be used as the oxidizing agent for the reaction, but it is not the best oxidizing agent.

Embodiment 3

[0044]The reaction steps and operation are the same as in Example 1, except that the difference from Example 1 is that the oxidizing agent is potassium persulfate. The reaction was stopped, and the target product 1a (4 mg, yield 4%) was obtained after post-treatment. It shows that potassium persulfate is not conducive to the reaction.

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Abstract

The invention discloses a method for synthesis of 2-imino oxazole derivatives having potential bioactive activity. The method comprises that 3, 3-diarylamino-2-propen-1-one, which is easy to prepare and has structural diversity and multiple reaction centers, is used as a raw material and undergoes an oxidative cyclization-Baldwin rearrangement reaction in air to produce a 2-imino oxazole derivative. Compared with the reported synthesis methods of 2-imino oxazole derivatives, the method provided by the invention utilizes easily available raw materials, can be simply operated and has mild reaction conditions and a high yield.

Description

technical field [0001] The invention discloses a method for synthesizing 2-imino oxazole derivatives with potential biological activity. Oxidative cyclization-Baldwin rearrangement reaction of 3,3-diarylamino-2-propen-1-one, which is easy to prepare, has structural diversity and multiple reaction centers, to synthesize 2-imine under air Oxazole derivatives. Compared with the reported synthesis method of 2-imino oxazole derivatives, the present invention has easy-to-obtain raw materials, simple operation, mild synthesis reaction conditions and high yield. Background technique [0002] Multi-substituted oxazoles and their derivatives are important intermediates for the synthesis of many natural products and drug molecules, and have a wide range of uses in the fields of industry, agriculture, and medicine. Due to their remarkable biopharmacological activity and unique plastic structure, the synthesis of multi-substituted oxazole derivatives has been widely concerned by chemis...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/38
CPCC07D263/38
Inventor 余正坤郭腾龙
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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